Question

Draw the major organic product formed when the compound shown below undergoes a reaction with (ch3)2culi in diethyl ether, followed by aqueous acid.

Answer 1

When the given alpha beta unsaturated carbony compound is treated with Organocuprate also called Gilman Reagent gives beta substituted carbonyl compound. As this reagent is soft nucleophile it adds to soft electrophile (beta carbon). Unlike Grignard Reagent which is hard nucleophile and adds to hard electrophile (carbonyl carbon) and produces corresponding alcohol. The reactions are as follow,